Lithium Hydroxide → 4-{[(5-Chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoic acid

HRID 1808187Notes

Reaction equation

HRID 1808187 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][S:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[C:13]([C:21]#[N:22])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1.[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[S:6][C:5]([NH:7][S:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:21]#[N:22])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86630782Methyl 4-{[(5-chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoate

Product 1

HCID 866307814-{[(5-Chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoic acidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-{[(5-chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoate (Preparation 21, 124 mg, 0.348 mmol, 1 eq) was dissolved in dioxane (2.5 ml): water (2.5 ml), lithium hydroxide (200 mg, 5 mmol, 14 eq) was added and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was diluted with water (5 ml), washed with ethyl acetate (10 ml), acidified with 2M HCl (10 ml), extracted into ethyl acetate (10 ml), dried over sodium sulphate, filtered and evaporated to yield the title compound as a brown solid (95 mg, 0.27 mmol, 79%).

Workup

  1. washwashed with ethyl acetate (10 ml)
  2. extractionextracted into ethyl acetate (10 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-741d72dff7ef4695a750efde2c386d14
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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